(E)-4-(3,5-dihydroxystyryl)phenyl benzoate | 1432450-03-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: (E)-4-(3,5-dihydroxystyryl)phenyl benzoate
• 英文别名: [4-[(E)-2-(3,5-dihydroxyphenyl)ethenyl]phenyl] benzoate
• CAS: 1432450-03-7
• 化学式: C₂₁H₁₆O₄
• 分子量: 332.356
• InChiKey: KXTWAMMJJKJEBZ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,5-二羟基苯甲酸 在 N-乙基吗啉 、 吡啶 、 1,3-bis-(1-adamantyl)imidazolinium tetrafluoroborate 、 氯化亚砜 、 二甲基硫 、 硫酸 、 三氟化硼乙醚 、 palladium diacetate 、 potassium carbonate 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 对二甲苯 、 甲苯 为溶剂， 反应 27.0h， 生成 (E)-4-(3,5-dihydroxystyryl)phenyl benzoate
  参考文献：
  名称：

  A new synthesis of 4′-resveratrol esters and evaluation of the potential for anti-depressant activity

  摘要：

  The 4'-ester analog of the disease preventative resveratrol 1 (RV), 4'-acetyl-RV 2 along with 4'-pivaloate 13 and benzoate 14 RV were synthesized. The previously developed palladium catalyzed decarbonylative Heck coupling was used to assemble the stilbene core together with 3,5-dibenzyl protected phenol intermediates that allowed for efficient coupling and deprotection using boron trifiuoride etherate. Studies with Long-Evans rats were performed to establish safety, toxicity, and behavioral parameters. In addition, the Porsalt forced-swim test was used to demonstrate anti-depressant activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.046

文献信息

• Selective esterification of the polyphenol resveratrol at the 4′-position
  作者：Mark J. Acerson、Merritt B. Andrus

  DOI：10.1016/j.tetlet.2013.12.019

  日期：2014.1

  Selective esterification of the polyphenol resveratrol was performed under thermodynamic conditions using NaH and acid anhydrides to directly access 4 '-esters. Standard conditions with acetyl chloride and pyridine showed poor selectivity, favoring esterification at the 3-position. The extended 4 '-phenolate anion is generated in preference to the 3-phenolate under the new anhydride-sodium hydride-DMSO conditions. Acylation occurs to access the 4 '-ester products with modest selectivity and yield with minimal formation of the 3-monoester, 3,5-diester, and triester products. (C) 2013 Elsevier Ltd. All rights reserved.
• A new synthesis of 4′-resveratrol esters and evaluation of the potential for anti-depressant activity
  作者：Mark J. Acerson、Kimberly M. Fabick、Yong Wong、Crystal Blake、Edwin D. Lephart、Merritt B. Andrus

  DOI：10.1016/j.bmcl.2013.03.046

  日期：2013.5

  The 4'-ester analog of the disease preventative resveratrol 1 (RV), 4'-acetyl-RV 2 along with 4'-pivaloate 13 and benzoate 14 RV were synthesized. The previously developed palladium catalyzed decarbonylative Heck coupling was used to assemble the stilbene core together with 3,5-dibenzyl protected phenol intermediates that allowed for efficient coupling and deprotection using boron trifiuoride etherate. Studies with Long-Evans rats were performed to establish safety, toxicity, and behavioral parameters. In addition, the Porsalt forced-swim test was used to demonstrate anti-depressant activity. (C) 2013 Elsevier Ltd. All rights reserved.